Education is what drives City Councilor John Connolly’s run against Boston Mayor Tom Menino. It’s a worthy issue with three daunting challenges: proving Menino has failed, convincing folks that Connolly has a better plan, and — if the first two tasks can be managed — finding enough voters who care.

Connolly announced his run at the end of February and was delighted with the immediate response. Within 24 hours, 600 volunteers had registered on his website. He knows the odds are long — “the entire city is questioning my sanity,” he tells me — but he thinks the state of Boston’s schools is the mayor’s weak spot.

In the 1990s, Menino promised big improvements. “Judge me harshly,” he said back then, and Connolly does. “The schools are marginally better but not where they should be,” he says. Excluding the notable successes of the city’s exam schools, “it’s been an abject failure.” Connolly promises a dramatic transformation.

Connolly’s thesis — that the system isn’t much improved — is debatable. By a variety of measures (dropout rates, graduation rates, and test scores), Boston’s schools are in fact better. Moreover, Connolly’s personal experience suggests not all is disaster. His daughter attends the Trotter Elementary School in Dorchester, once a failing school. Connolly enthuses about the education she receives. Asked if Menino deserves credit, he demurs, mentioning 2010 state education reform as well as saying that Trotter is a rare exception. Yet a majority of parents in systemwide BPS surveys agree with the statement, “This school is a good place for my child to learn.”

Fundamentally, though, Connolly is right: Good isn’t great. Boston’s overall test scores, for instance, are still well below state averages. But how does one get from today’s results to some sort of educational nirvana?

Connolly ticks off five changes. First, he’d cut the central office budget, putting the saved money into classrooms. Second, he’d lengthen the school year. Next, he’d work harder to recruit and train talented principals. He’d also make sure every school had guidance counselors, social workers, and nurses. Finally, he’d devote more money to fixing up Boston’s “crumbling” school buildings.

It is, to be blunt, an uninspiring list. Connolly focuses on tried-and-true inputs (additional spending, longer days, better training, more staff, and nicer buildings) that haven’t been shown to much affect results. A better approach would be to set goals (90 percent of all students are proficient or better by 2017, for example). As well, Connolly’s proposals seem subject to the same critique that many make of Menino — they’re incremental. Big, daring ideas that might truly improve outcomes are missing. How about converting all schools to charter schools? Reforming the curriculum to a hybrid online/brick-and-mortar blend (as Rocketship Schools is doing in California)? Significantly expanding early childhood education? Or all of these and more?

Connolly certainly isn’t holding back because he’s trying to curry favor with the city’s teachers’ unions; he knows he won’t get it. “The school department is dysfunctional to its core,” he argues. If so, what is needed — and what might make this a bracing campaign — is a plan to remake the system altogether.

Even so, it’s not clear that education alone can carry Connolly to victory. The conventional wisdom is that more voters don’t care about education than do, and so as a close-to-single-issue candidate (“I care about other issues, but I’ll talk most about schools”) he will have a hard time prizing away those happy with Menino’s successes on everything from crime to street cleaning to residential resurgence. Indeed, some of Connolly’s proposals — such as spending more on school buildings — will inevitably mean spending less on capital projects (such as playgrounds and parks) dear to others.

Then too, education’s greatest appeal, one would think, would be to those who can’t afford private or parochial schools — which is to say, the city’s minority communities. Yet it’s those areas where Menino holds his strongest sway — his focus on neighborhood revitalization has won him plaudits and loyalty.

No question, Connolly is sincere on the issue; he’s a former teacher and education has been his passion since he was first elected in 2007. But turning this sincerity into victory requires something bolder and more persuasive than what he now offers up.

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